EP1587871B1 - Preformed compositions in shaped form - Google Patents
Preformed compositions in shaped form Download PDFInfo
- Publication number
- EP1587871B1 EP1587871B1 EP04705983A EP04705983A EP1587871B1 EP 1587871 B1 EP1587871 B1 EP 1587871B1 EP 04705983 A EP04705983 A EP 04705983A EP 04705983 A EP04705983 A EP 04705983A EP 1587871 B1 EP1587871 B1 EP 1587871B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- weight
- preformed
- sulfur
- containing polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 163
- 229920000642 polymer Polymers 0.000 claims abstract description 46
- 229910052618 mica group Inorganic materials 0.000 claims abstract description 29
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000011593 sulfur Substances 0.000 claims abstract description 27
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 27
- 239000004952 Polyamide Substances 0.000 claims abstract description 26
- 239000010445 mica Substances 0.000 claims abstract description 26
- 229920002647 polyamide Polymers 0.000 claims abstract description 26
- 239000000945 filler Substances 0.000 claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 20
- 229920001021 polysulfide Polymers 0.000 claims description 20
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 19
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical group O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 12
- 239000000446 fuel Substances 0.000 claims description 11
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 9
- 229910021485 fumed silica Inorganic materials 0.000 claims description 9
- 239000004005 microsphere Substances 0.000 claims description 9
- 239000004014 plasticizer Substances 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
- 238000007789 sealing Methods 0.000 claims description 8
- 239000005011 phenolic resin Substances 0.000 claims description 6
- 229920001568 phenolic resin Polymers 0.000 claims description 6
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 5
- 229920000647 polyepoxide Polymers 0.000 claims description 5
- 239000002318 adhesion promoter Substances 0.000 claims description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 description 22
- 239000000565 sealant Substances 0.000 description 13
- 239000000654 additive Substances 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 10
- 238000002156 mixing Methods 0.000 description 8
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 8
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 8
- 239000004408 titanium dioxide Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000005077 polysulfide Substances 0.000 description 4
- 150000008117 polysulfides Polymers 0.000 description 4
- 229920006295 polythiol Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- -1 Bisphenol-A epoxides Chemical class 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 229920006122 polyamide resin Polymers 0.000 description 3
- 239000004587 polysulfide sealant Substances 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 3
- 229960002447 thiram Drugs 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- 239000005083 Zinc sulfide Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 2
- LHJQIRIGXXHNLA-UHFFFAOYSA-N calcium peroxide Chemical compound [Ca+2].[O-][O-] LHJQIRIGXXHNLA-UHFFFAOYSA-N 0.000 description 2
- 235000019402 calcium peroxide Nutrition 0.000 description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
- 239000002828 fuel tank Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 238000000518 rheometry Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229910052984 zinc sulfide Inorganic materials 0.000 description 2
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- XSVSPKKXQGNHMD-UHFFFAOYSA-N 5-bromo-3-methyl-1,2-thiazole Chemical compound CC=1C=C(Br)SN=1 XSVSPKKXQGNHMD-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 1
- 239000004343 Calcium peroxide Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 241000761557 Lamina Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910001069 Ti alloy Inorganic materials 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- FKIQSOGFDBALHA-UHFFFAOYSA-L aluminum trimagnesium potassium dioxido(oxo)silane oxygen(2-) difluoride Chemical compound [O--].[F-].[F-].[Mg++].[Mg++].[Mg++].[Al+3].[K+].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O FKIQSOGFDBALHA-UHFFFAOYSA-L 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 150000001553 barium compounds Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052626 biotite Inorganic materials 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007739 conversion coating Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- YGANSGVIUGARFR-UHFFFAOYSA-N dipotassium dioxosilane oxo(oxoalumanyloxy)alumane oxygen(2-) Chemical compound [O--].[K+].[K+].O=[Si]=O.O=[Al]O[Al]=O YGANSGVIUGARFR-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- DLINORNFHVEIFE-UHFFFAOYSA-N hydrogen peroxide;zinc Chemical compound [Zn].OO DLINORNFHVEIFE-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000013339 in-process testing Methods 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052627 muscovite Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052628 phlogopite Inorganic materials 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006009 resin backbone Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229940105296 zinc peroxide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/02—Polythioethers; Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/04—Polysulfides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
- C09K3/1012—Sulfur-containing polymers, e.g. polysulfides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2381/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen, or carbon only; Polysulfones; Derivatives of such polymers
- C08J2381/02—Polythioethers; Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
- C08L2666/16—Addition or condensation polymers of aldehydes or ketones according to C08L59/00 - C08L61/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
- C08L2666/22—Macromolecular compounds not provided for in C08L2666/16 - C08L2666/20
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/66—Substances characterised by their function in the composition
- C08L2666/72—Fillers; Inorganic pigments; Reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Definitions
- the present invention relates to preformed compositions in shaped form and the use of preformed compositions for sealing apertures.
- Polysulfide polymers are known in the art. The production of polysulfide polymers is characterized by Fettes and Jorczak, Industrial and Engineering Chemistry, November 1950, on pages 2,217-2,223 . The commercial use of polysulfide polymers in the manufacture of sealants for aerospace applications has long been known and commercially used. Polysulfide sealants have been used to seal aircraft exterior fuselage because of the high tensile strength, high tear strength, thermal resistance and resistance to high ultraviolet light. Polysulfide sealants have been used to seal aircraft fuel tanks because of the resistance to fuel and adhesion upon exposure to fuel.
- Polysulfide sealants are generally applied by extrusion using a caulking gun. Such a process may be efficient for permanent panels installed on the aircraft fuselage.
- extruding a sealant to seal apertures in the fuselage of an aircraft can require a significant amount of additional effort than for extruding the same sealant to permanent panels.
- the interior perimeter of the access door opening is masked and the exterior perimeter of the access door is coated with a release agent prior to extruding the sealant to the masked area of the access door opening to avoid sealing an access door shut. The access door is put in place and clamped down to force the excess sealant around the access door.
- the sealant is allowed to cure and the sealant around the access door.
- the sealant is allowed to cure and the excess sealant is trimmed away. This process is time intensive and can add significant labor to servicing aircraft with many access doors. Some aircraft can have as many as a hundred or more access doors that are used to cover sensitive equipment or fittings that must be periodically accessed.
- a composition comprises (a) a sulfur-containing polymer, and (b) a blend of fillers, wherein the blend comprises substantially equal amounts by weight of mica and polyamide.
- a method for sealing an aperture comprises (a) applying a preformed composition comprising a sulfur-containing polymer in tape form to cover the aperture, and (b) curing the composition while in place covering the aperture so as to seal the aperture.
- a preformed composition suitable for sealing apertures comprises a sulfur-containing polymer in shaped form.
- preformed refers to a composition that can be prepared into a particular shape for ease of packaging, storage, and/or application.
- a composition that is preformed can be reshaped into any shape either intentionally or as a result of shipping and/or handling.
- shaped form refers to a configuration such that the thickness of the preformed composition is substantially less than the lateral dimension and includes tapes, sheets and cut-out or gasket forms.
- the "shaped form” can be in the form of a tape meaning a narrow shape, strip, or band that can be stored as rolls, coils, or strips.
- the "shaped form” can also be die-cut to the dimensions of the aperture to be sealed.
- sealant refers to compositions that have the ability to resist atmospheric conditions such as moisture and temperature and at least partially block the transmission of materials such as water, fuel, and other liquids and gasses. Sealants often have adhesive properties, but are not simply adhesives that do not have the blocking properties of a sealant.
- elongated aperture refers to an opening in which the length is at least three-times the width.
- the sulfur-containing polymers useful in the practice of the invention are polysulfide polymers that contain multiple sulfide groups, i.e., -S-, in the polymer backbone and/or in the terminal or pendent positions on the polymer chain.
- Such polymers are described in U.S. Patent No. 2,466,963 wherein the disclosed polymers have multiple -S-S-linkages in the polymer backbone.
- Other useful polysulfide polymers are those in which the polysulfide linkage is replaced with a polythioether linkage, i.e., -[-CH 2 -CH 2 -S-CH 2 -CH 2 -] n - where n is from 8 to 200 as described in U.S.
- Patent No. 4,366,307 The polysulfide polymers can be terminated with non-reactive groups such as alkyl, although preferably the polysulfide polymers contain reactive groups in the terminal or pendent positions. Typical reactive groups are thiol, hydroxyl, amino, and vinyl.
- Such polysulfide polymers are described in the aforementioned U.S. Patent No. 2,466,963 , U.S. Patent No. 4,366,307 , and U.S. Patent No. 6,372,849 .
- Such polysulfide polymers can be cured with curing agents that are reactive with the reactive groups of the polysulfide polymer.
- two-component curable compositions are preferred to the one-component curable compositions because the two-component compositions provide the best rheology for application and exhibit desirable physical and chemical properties in the resultant cured composition.
- the two components are referred to as the base composition and the curing agent composition.
- the base composition comprises polysulfide polymers, oxidizing agents, additives, fillers, plasticizers, organic solvents and combinations thereof.
- the curing agent composition comprises curing agents, plasticizers, additives, fillers and combinations thereof.
- the sulfur-containing polymers of the invention typically have number average molecular weights ranging from 500 to 8,000 Daltons, and more typically from 1,000 to 4,000 Daltons, as determined by gel permeation chromatography using a polystyrene standard.
- the sulfur-containing polymers For sulfur-containing polymers that contain reactive functional groups, the sulfur-containing polymers have average functionalities ranging from 2.05 to 3.0 and more typically from 2.1 to 2.6. A specific average functionality can be achieved by suitable selection of reactive ingredients.
- suitable sulfur-containing polymers are those available from PRC-DeSoto International, Inc. under the trademark PERMAPOL ® , specifically, PERMAPOL P-3.1E ® or PERMAPOL P-3 ® .
- the preformed composition of the present invention comprises a curing agent for the sulfur-containing polymer.
- the curing agent is reactive at 10°C to 80°C.
- the term "reactive" means capable of chemical reaction and includes any level of reaction from partial to complete reaction of a reactant.
- a curing agent is reactive when it provides for cross-linking or gelling of a sulfur-containing polymer.
- the preformed composition comprises a curing agent that contains oxidizing agents that oxidize terminal mercaptan groups of the sulfur-containing polymer to form disulfide bonds.
- Useful curing agents include lead dioxide, manganese dioxide, calcium dioxide, sodium perborate monohydrate, calcium peroxide, zinc peroxide, and dichromate.
- the term "curing agent” refers to any material that can be added to a sulfur-containing polymer to accelerate the curing or gelling of the sulfur-containing polymer. Curing agents are also known as accelerators, catalysts or cure pastes.
- preformed compositions of the present invention comprise one or more curing agents that contain reactive functional groups that are reactive with the functional groups attached to the sulfur-containing polymer.
- Useful curing agents include polythiols, such as polythioethers, for curing vinyl-terminated polymers; polyisocyanates such as isophorone diisocyanate, hexamethylene diisocyanate, and mixtures and isocyanurate derivatives thereof for curing thiol-, hydroxyl- and amino- terminated polymers; and, polyepoxides for curing amine- and thiol-terminated polymers.
- polyepoxides examples include hydantoin diepoxide, Bisphenol-A epoxides, Bisphenol-F epoxides, Novolac-type epoxides, aliphatic polyepoxides, and epoxidized unsaturated and phenolic resins.
- polyepoxide refers to a material having a 1,2-epoxy equivalent greater than one and includes monomers, oligomers, and polymers.
- preformed compositions of the present invention comprise additives.
- additive refers to a non-reactive component in the preformed composition that provides a desired property.
- examples of additives include micas and polyamides.
- Mica is a silicate characterized by basal cleavage that imparts flexibility to laminas. Micas include natural muscovite, phlogopite, and biotite, as well as synthetic fluorophlogopite and barium disilicic. Preparation of synthetic micas is described in Encyclopedia of Chemical Technology, Vol. 13, pp. 398-424, John Wiley & Sons (1967 ). Mica provides flexibility and pliability to the preformed composition and reduces the tack.
- Polyamide powder provides viscosity and reduces the tack of the preformed composition.
- Polyamide resins can be produced by the condensation reaction of dimerized fatty acids, such as dimerized linoleic acid, with lower aliphatic polyamines, such as for example, ethylene diamine or diethylene triamine, so that the final product has multiple amide groups in the resin backbone.
- dimerized fatty acids such as dimerized linoleic acid
- lower aliphatic polyamines such as for example, ethylene diamine or diethylene triamine
- additives useful in the preformed compositions of the present invention include those commonly used in the art, such as carbon black and calcium carbonate.
- Other additives include fumed silica, microspheres, titanium dioxide, chalks, alkaline blacks, cellulose, zinc sulfide, heavy spar, alkaline earth oxides, and alkaline earth hydroxides.
- Additives also include high band gap materials such as zinc sulfide and inorganic barium compounds.
- plasticizers plasticizers. Plasticizers that are useful include phthalate esters, chlorinated paraffins, and hydrogenated terphenyls.
- the preformed composition further comprises an organic solvent, such as a ketone or an alcohol, for example methyl ethyl ketone and isopropyl alcohol, or a combination thereof.
- an organic solvent such as a ketone or an alcohol, for example methyl ethyl ketone and isopropyl alcohol, or a combination thereof.
- mica and polyamide together form 10% by weight to 50% by weight of the total weight of the preformed composition with substantially equal amounts of mica and polyamide.
- substantially equal means that the amount of mica and the amount of polyamide are present in an amount of less than 5% of each other. Amounts greater than 50% by weight can be difficult to mix.
- the amount of mica can range from 5% by weight to 25% by weight and the amount of polyamide from 5% by weight to 25% by weight.
- the amount of mica ranges from 10% by weight to 20% by weight and the amount of polyamide ranges from 10% by weight to 20% by weight of the total weight of the preformed composition. Adding only mica or only polyamide impacts the rheology of the uncured preformed composition, but generally does not change the properties of the preformed composition when cured such as tensile elongation, compression, fuel resistance and thermal resistance.
- the base composition and curing agent composition are proportioned to 100 parts by weight of base composition and 2 to 12 parts by weight of curing agent composition.
- the equivalent ratio of curing agent to sulfur-containing polymer should range from 0.5:1 to 2.0:1
- additives other than mica and polyamide comprise up to 30% by weight of the total weight of the preformed composition.
- the preformed compositions of the present invention are prepared as separate components referred to as the base composition and the curing agent composition prior to mixing and application.
- a base composition can be prepared by batch mixing a sulfur-containing polymer, mica, polyamide, and other additives in a double planetary mixer under vacuum.
- suitable mixing equipment include a kneader extruder, sigma mixer, or double "A" arm mixer.
- a sulfur-containing polymer, 2-mercaptoethanol, and a plasticizer are charged to the double planetary mixer and mixed under vacuum for 6 to 8 minutes.
- Silica is then mixed until cut in followed by the addition of titanium dioxide that is mixed until cut in.
- Calcium carbonate is then charged and mixed until cut in, followed by the addition of mica that is mixed until cut in.
- Polyamide is then charged and mixed until cut in, and the mixture is then mixed for 3 to 15 minutes under vacuum.
- Microspheres are then charged and mixed until cut in.
- the mixture is then mixed for an additional 15 to 20 minutes under a vacuum of 27 inches of mercury or greater.
- In-process testing is performed and if the mixture is too tacky, equal amounts of mica and polyamide powder are added and mixed under vacuum to reduce tack.
- the base composition is then extruded from the mixer using a high pressure piston ram.
- the curing agent composition can be prepared by batch mixing the curing agent and other additives.
- 75% of the total plasticizer such as partially hydrogenated terphenyl and an accelerant such as a dipentamethylene/thiuram/polysulfide mixture are mixed in a single-shaft anchor mixer.
- Molecular sieve powder is then added and mixed for 2 to 3 minutes.
- Fifty percent of the total manganese dioxide is then mixed until cut in.
- Stearic acid, sodium stearate, and the remaining plasticizer are then mixed until cut in followed by the remaining 50% of the manganese dioxide which is mixed until cut in.
- Silica is then mixed until cut in. If the mixture is too thick a surfactant may be added to increase wetting.
- the curing agent composition is then mixed for 2 to 3 minutes, passed over a three-roll paint mill to achieve a grind, and returned to the single-shaft anchor mixer and mixed for an additional 5 to 10 minutes.
- the curing agent composition is then removed from the mixer with a piston ram and placed into storage containers and aged for at least 5 days prior to combining with the base composition.
- the base composition and curing agent composition are mixed together to form the preformed composition.
- the base composition and curing agent composition are combined in the desired ratio using meter mix equipment fitted with a dynamic mix head. Pressure from the meter mix equipment forces the base and curing agent compositions through the dynamic mix head and an extrusion die.
- the preformed composition is extruded into a laminar form including a tape or sheet.
- the preformed composition in sheet form can be cut to any desired shape such as defined by the dimensions of an aperture to be sealed.
- the shaped form can be coiled with release paper separating each ring for packaging purposes.
- the shaped form is then refrigerated by placing the shaped form on a bed of dry ice and placing another layer of dry ice on the top of the shaped form.
- the shaped form is refrigerated immediately after mixing the base composition and the curing agent composition.
- the shaped form remains exposed to the dry ice for 5 to 15 minutes and is then placed at a storage temperature of -40°C or lower.
- the term "refrigerated” refers to reducing the temperature of the preformed composition so as to retard and/or stop the curing of the preformed composition.
- the preformed composition in shaped form is refrigerated below -40°C.
- the temperature of the preformed composition is raised to a use temperature ranging from 4°C to 32°C (40°F to 90°F) prior to application. This is done such that the preformed composition reaches use temperature for no more than 10 minutes prior to application.
- the preformed composition in shaped form can be used to seal an aperture between a removable access panel and the surface adjacent to the perimeter of an opening in an aircraft fuselage.
- Adhesion promoter is first brushed on the perimeter of the access panel opening after the surface has been cleaned with a cleaning solvent such as Desociean ® .
- the surface of the access panel is then cleaned and coated with a release agent prior to applying the preformed composition.
- the preformed composition in shaped form is manually applied to the surface adjacent to the perimeter of the access panel opening, to the surface adjacent to the perimeter of the access panel, or to both.
- the access panel is then put in place and clamped down forcing the excess preformed composition around the edges of the access panel.
- Excess preformed composition is easily removed by using, for example, a flat surface.
- Excess preformed composition can be removed either prior to curing or after the preformed composition has cured, and preferably after the preformed composition cures.
- the integrity, moisture resistance and fuel resistance of the seal resulting from application of preformed compositions of the present invention can be evaluated by performing the tests identified in specification MMS 332.
- An acceptable seal will be tight and resistant to moisture and aircraft fuel.
- Example 1 the following materials were mixed in the proportions according to Table I to form the base composition: Thioplast ® polysulfide polymer from Akzo-Nobel, 2-mercaptoethanol from BASF, Terminol ® partially hydrogenated terphenyl plasticizer from Solutia, phenolic resin from PRC-DeSoto International, Inc., Cab-O-Sil ® fumed silica from Cabot Corporation, titanium dioxide, Socal ® or Winnofil ® precipitated calcium carbonate from Solvay, mica from ACME-Hardesty Company, Orgasol ® polyamide powder from Atofina, and Expancel ® microspheres from Akzo-Nobel.
- the following materials were mixed in the amounts according to Table II to form the curing agent composition: manganese dioxide from Eagle Picher, partially hydrogenated terphenyl, stearic acid, fumed silica, sodium stearate from Witco Chemicals, molecular sieve powder to remove excess moisture from the curing agent, and dipentamethylene/thiuram/polysulfide mixture from Akrochem Corporation to accelerate the cure.
- One hundred parts by weight of base composition and 10 parts by weight of curing agent composition were mixed to prepare the preformed composition. After mixing, the preformed composition was extruded into a tape form and refrigerated at -40°C.
- the surface adjacent to the perimeter of an access panel was first coated with low VOC epoxy primer according to specification MMS-423 and cured. The surface was cleaned and then coated with adhesion promoters PR-148 ® or PR-184 ® from PRC-DeSoto International, Inc.
- the access panel was made from AMS-T-9046 titanium alloy. After the refrigerated preformed composition equilibrated to use temperature, 4°C to 32°C (40°F to 90°F), the preformed composition in tape form was manually applied to the surface adjacent to the perimeter of the access panel. The access panel was put in place to cover the access opening and clamped down, forcing the excess preformed composition around the edges of the access panel to fill the aperture. Excess preformed composition was easily removed. After 3 to 4 hours at a temperature of 4°C to 32°C (40°F to 90°F), a tight seal, resistant to moisture and aircraft fuel, resulted.
- the preformed composition as described above was also applied to an access panel made from aluminum that was treated with a conversion coating meeting specification MIL-C-5541 and then coated with fuel tank coating meeting specification AMS-C-27725. After 3 to 4 hours at a temperature of 4°C to 32°C (40°F to 90°F), a tight seal, resistant to moisture and aircraft fuel, resulted.
- a polythioether polymer Permapol P-3.1e ® from PRC-DeSoto International, Inc., Glendale, California, Bisphenol-A epoxy resin, and triethylene diamine were combined in the proportions according to Table III to form a thiol-terminated polymer adduct.
- the compounds in Table II were blended and heated to 71 °C (160°F) and mixed at 71 °C for one hour. The mixture was then heated for 14 to 24 hours at 60°C (140°F) without mixing to form a thiol-terminated polymer adduct.
- Thiol-terminated polymer adduct, triethylenediamine, partially hydrogenated terphenyl, titanium dioxide, calcium carbonate, mica, polyamide powder, and microspheres were mixed in the proportions according to Table IV to form the base composition.
- the curing agent composition was formed by mixing liquid epoxy resin from Shell Chemical, partially hydrogenated terphenyl, carbon black from Cabot Corporation, fumed silica, calcium carbonate, mica, polyamide powder, and microspheres in the proportions according to Table V.
- 100 parts by weight of base composition and 10.9 parts by weight of curing agent composition were mixed to prepare a preformed composition with an epoxy-to-thiol ratio of 1.53:1.
- a mix ratio of 100 parts by weight of base composition and 11.67.parts by weight of curing agent composition were mixed to prepare a preformed composition with an epoxy-to-thiol ratio of 1.64:1.
- the preformed composition was subsequently extruded into a tape form and refrigerated to -62°C. After equilibrating to use temperature, the preformed compositions were applied to the surfaces adjacent to the perimeter of access panels as described in Example 1. After 3 to 4 hours at a temperature of 4°C to 32°C (40°F to 90°F), tight seals, resistant to moisture and aircraft fuel, resulted.
- Example 3 four additional base compositions using different amounts of the components of Example 1 were prepared according to Table VI.
- the base compositions of Table VI were independently mixed with the curing agent composition of Example 1. As in Example 1, 100 parts by weight of the base composition was mixed with 10 parts by weight of the curing agent composition to prepare the preformed composition. The preformed composition was extruded in tape form, refrigerated, equilibrated to use temperature and applied to an access panel as described in Example 1. After 3 to 4 hours at a temperature of 4°C to 32°C (40°F to 90°F) a tight seal, resistant to moisture and aircraft fuel, resulted.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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PCT/US2004/002263 WO2004067635A1 (en) | 2003-01-30 | 2004-01-28 | Preformed compositions in shaped form |
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EP1587871B1 true EP1587871B1 (en) | 2009-10-07 |
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EP (1) | EP1587871B1 (zh) |
JP (2) | JP4209426B2 (zh) |
KR (1) | KR100695585B1 (zh) |
CN (1) | CN1771293B (zh) |
AT (1) | ATE444993T1 (zh) |
AU (1) | AU2004207826B2 (zh) |
BR (1) | BRPI0407130B1 (zh) |
CA (1) | CA2514428C (zh) |
DE (1) | DE602004023479D1 (zh) |
DK (1) | DK1587871T3 (zh) |
ES (1) | ES2331696T3 (zh) |
IL (1) | IL169903A (zh) |
MX (1) | MXPA05008069A (zh) |
RU (1) | RU2301820C2 (zh) |
WO (1) | WO2004067635A1 (zh) |
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US7067612B2 (en) * | 2003-01-30 | 2006-06-27 | Prc-Desoto International, Inc. | Preformed compositions in shaped form |
US20050245695A1 (en) * | 2004-04-30 | 2005-11-03 | Cosman Michael A | Polymer blend and compositions and methods for using the same |
UA81885C2 (uk) * | 2004-09-08 | 2008-02-11 | Прк-Дэсото Интэрнэшнл, Инк. | Попередньо сформовані композиції в профільованій формі, що містять полімерні суміші, та спосіб закладання апертури |
US7498384B2 (en) * | 2005-02-04 | 2009-03-03 | Ppg Industries Ohio, Inc. | Multi-component epoxy-amine primer systems comprising a polythioether |
US20070096396A1 (en) * | 2005-10-27 | 2007-05-03 | Sawant Suresh G | Dimercaptan terminated polythioether polymers and methods for making and using the same |
US7879955B2 (en) * | 2007-05-01 | 2011-02-01 | Rao Chandra B | Compositions including a polythioether |
US9080004B2 (en) * | 2010-10-07 | 2015-07-14 | Prc-Desoto International, Inc. | Diethylene glycol monomethyl ether resistant coating |
US8541513B2 (en) * | 2011-03-18 | 2013-09-24 | Prc-Desoto International, Inc. | Terminal-modified difunctional sulfur-containing polymers, compositions thereof and methods of use |
US8729216B2 (en) | 2011-03-18 | 2014-05-20 | Prc Desoto International, Inc. | Multifunctional sulfur-containing polymers, compositions thereof and methods of use |
SI23731A (sl) | 2011-05-09 | 2012-11-30 | CBS@INĹ TITUT@@celovite@gradbene@rešitve@@d@o@o | Lepilno tesnilna masa prednostno za uporabo v panelu za uporabo v gradbeništvu |
US9181628B2 (en) * | 2011-09-14 | 2015-11-10 | Prc-Desoto International, Inc. | Coating/sealant systems, aqueous resinous dispersions, and methods of electrocoating |
US20130082214A1 (en) * | 2011-09-16 | 2013-04-04 | Prc-Desoto International, Inc. | Conductive sealant compositions |
US9484123B2 (en) * | 2011-09-16 | 2016-11-01 | Prc-Desoto International, Inc. | Conductive sealant compositions |
US8901256B2 (en) * | 2012-01-12 | 2014-12-02 | Prc-Desoto International, Inc. | Polythioethers, moisture curable compositions and methods for their manufacture and use |
DE102012205951B4 (de) * | 2012-04-12 | 2016-09-01 | Chemetall Gmbh | Dichtmassen-System, ungehärtete Grundmasse und Mischung, Härter, Verfahren zum Beschichten eines Substrates und Verwendung eines Dichtmassen-Systems |
US9650552B2 (en) * | 2013-03-15 | 2017-05-16 | Prc-Desoto International, Inc. | Energy curable sealants |
US9518197B2 (en) | 2014-03-07 | 2016-12-13 | Prc-Desoto International, Inc. | Cure-on-demand moisture-curable urethane-containing fuel resistant prepolymers and compositions thereof |
US9951252B2 (en) | 2015-08-10 | 2018-04-24 | Prc-Desoto International, Inc. | Moisture-curable fuel-resistant sealant systems |
CN105440682A (zh) * | 2015-12-23 | 2016-03-30 | 佛山华清智业环保科技有限公司 | 一种环保塑胶板 |
US10370561B2 (en) | 2016-06-28 | 2019-08-06 | Prc-Desoto International, Inc. | Urethane/urea-containing bis(alkenyl) ethers, prepolymers prepared using urethane/urea-containing bis(alkenyl) ethers, and uses thereof |
JP2019530784A (ja) * | 2016-10-06 | 2019-10-24 | スリーエム イノベイティブ プロパティズ カンパニー | 硬化性組成物及び関連方法 |
EP3555178A1 (en) * | 2016-12-14 | 2019-10-23 | 3M Innovative Properties Company | Sealant tape |
US10597565B2 (en) | 2017-07-07 | 2020-03-24 | Prc-Desoto International, Inc. | Hydraulic fluid and fuel resistant sealants |
US11098222B2 (en) | 2018-07-03 | 2021-08-24 | Prc-Desoto International, Inc. | Sprayable polythioether coatings and sealants |
US11015097B2 (en) | 2019-03-06 | 2021-05-25 | Prc-Desoto International, Inc. | Chemically resistant sealant compositions and uses thereof |
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KR100695585B1 (ko) | 2007-03-14 |
CA2514428C (en) | 2008-10-07 |
KR20050105988A (ko) | 2005-11-08 |
ES2331696T3 (es) | 2010-01-13 |
RU2301820C2 (ru) | 2007-06-27 |
DK1587871T3 (da) | 2010-01-18 |
CN1771293A (zh) | 2006-05-10 |
MXPA05008069A (es) | 2005-09-21 |
IL169903A (en) | 2011-02-28 |
US20040152866A1 (en) | 2004-08-05 |
AU2004207826B2 (en) | 2006-11-16 |
RU2005127205A (ru) | 2006-01-27 |
US7067612B2 (en) | 2006-06-27 |
CA2514428A1 (en) | 2004-08-12 |
ATE444993T1 (de) | 2009-10-15 |
AU2004207826A1 (en) | 2004-08-12 |
JP2008156650A (ja) | 2008-07-10 |
BRPI0407130A (pt) | 2006-01-10 |
JP4209426B2 (ja) | 2009-01-14 |
DE602004023479D1 (de) | 2009-11-19 |
CN1771293B (zh) | 2010-05-26 |
IL169903A0 (en) | 2009-02-11 |
JP2006513314A (ja) | 2006-04-20 |
WO2004067635A1 (en) | 2004-08-12 |
EP1587871A1 (en) | 2005-10-26 |
BRPI0407130B1 (pt) | 2014-02-11 |
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